Journal
JOURNAL OF COMPUTATIONAL CHEMISTRY
Volume 40, Issue 19, Pages 1772-1779Publisher
WILEY
DOI: 10.1002/jcc.25830
Keywords
greener catalyst; external electric field; anti- or Markovnikov hydroboration
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Funding
- National Science Foundation of China [NSFC 21473026, 21503040]
- Science and Technology Development Planning of Jilin Province [20140101046JC]
- China Postdoctoral Science Foundation [2014M560227]
- Fundamental Research Funds for the Central Universities [2412018ZD008]
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Usually, an extra catalyst (for example, the transition metal complexes) need to be used in catalyzing hydroboration, which involved the cost, environment, and so forth. Here, a greener and controllable catalyst-external electric field (EEF) was used to study its effect on hydroboration of N-(4-methylbenzyl)aniline (PhNCHPhMe) with pinacolboane (HBPin). The results demonstrated that EEF could affect the barrier heights of both two pathways of this reaction. More significantly, flipping the direction of EEF could modify the reaction mechanism to induce a dominant inverse hydroboration at some field strength. That is to say, oriented EEF is a controlling switch for the anti- or Markovnikov hydroboration reaction of imines. This investigation is meaningful for the exploration of greener catalyst for chemistry reaction and guide a new method for the Markovnikov hydroboration addition. (c) 2019 Wiley Periodicals, Inc.
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